Ortho and Para Substituted Derivatives of Benzotrifluoride

Jones, Reuben G.

doi:10.1021/ja01202a028

Cited by 85 publications

(26 citation statements)

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“…It should be noted that when there is a trifluoromethyl group in the ortho or para position of the hydrosulphonyl group of 2, the trifluoromethyl group itself will be hydrolyzed at the same time when the cyanogroup is hydrolyzed, however when the trifluoromethyl group is at the meta position of the hydrosulphonyl group, the hydrolysis of trifluoromethyl group does not happen, which has been confirmed by the final compounds. This is in agreement with an early report by Jones in 1947 [14]. The synthesis and characterizations of the intermediates 2 and 3 are detailed in the supplementary material.…”

Section: Synthesis Of the Ptb Derivativessupporting

confidence: 91%

Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives

Zhou

Yang

et al. 2019

European Journal of Medicinal Chemistry

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a b s t r a c tSince pyrithiobac (PTB) is a successful commercial herbicide with very low toxicity against mammals, it is worth exploring its derivatives for an extensive study. Herein, a total of 35 novel compounds were chemically synthesized and single crystal of 6e6 was obtained to confirm the molecular structure of this family of compounds. The novel PTB derivatives were fully evaluated against various biological platforms. From the bioassay results, the best AHAS inhibitor 6e22 displayed weaker herbicidal activity but stronger anti-Candida activity than PTB did. For plant pathogenic fungi, 6e26 showed excellent activity at 50 mg/L dosage. Preliminary insecticidal activity and antiviral activity were also observed for some title compounds. Strikingly, 6e5 exhibited a promising inhibitory activity against SARS-CoV M pro with IC 50 of 4.471 mM and a low cellular cytotoxicity against mammalian 293 T cells. Based on the results of molecular modeling, HOMO-1 was considered to be a factor that affects AHAS inhibition and a possible binding mode of 6e5 with SARS-CoV M pro was predicted. This is the first time that PTB derivatives have been studied as biological agents other than herbicides. The present research hence has suggested that more attentions should be paid to compounds belonging to this family to develop novel agrochemicals or medicines.

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Section: Synthesis Of the Ptb Derivativessupporting

confidence: 91%

Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives

Zhou

Yang

et al. 2019

European Journal of Medicinal Chemistry

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“…[22,23] Similar transformations of trifluoromethyl groups by two-step nucleophilic substitutions have been reported for 4-(trifluoromethyl)ani-line, [24,25] 4-(nonofluorobutyl)aniline, [26] 2-and 3-(trifluoromethyl)indole, [27,28] and 5-amino-2-chloro-4-(trifluoromethyl)thiazole. [29] The irreversible inhibition of decarboxylases, transaminases, and racemases by a variety of β-fluoroamines also involves the elimination of hydrogen fluoride and subsequent binding to the enzyme through a cysteine residue.…”

Section: Introductionsupporting

confidence: 65%

Fluorine-Sacrificial Cyclizations as an Access to 5-Fluoropyrazoles

Volle

Schlosser

2000

Eur. J. Org. Chem.

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Methyl 3‐methoxy‐2‐trifluoromethylacrylate 1, readily prepared by Wittig reaction from methyl 3,3,3‐trifluoropyruvate, has been treated with a number of aryl‐ (or hetaryl‐) hydrazines. Under mild base‐catalysis, the resulting 3‐hydrazinoacrylates 6 undergo consecutive hydrogen fluoride elimination and intramolecular nucleophilic addition to afford methyl 1‐(het)aryl‐5‐fluoropyrazole‐4‐carboxylates 7. 5‐Aminopyrazoles 8 have been obtained by direct reaction of the ester 7a with a lithium amide, whereas 5‐fluoro‐1‐phenylpyrazole‐4‐carboxamides 10 have been formed by condensation of the 5‐fluoro‐1‐phenylpyrazole‐4‐carboxylic acid 9 with amines.

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“…Two papers published 40 years earlier also showed an abnormal behavior of the trifluoromethyl group in alkaline medium. One such case involved the reaction of 0-and p-substituted benzotrifluorides (Jones, 1947) with base: \ 0 : ; +3NaOH a 0-+ 3NaFi 3 H20…”

Section: The Chemical Modification Of Agarose With Cyanogen Bromide Amentioning

confidence: 99%

Cyanogen bromide and tresyl chloride chemistry revisited: The special reactivity of agarose as a chromatographic and biomaterial support for immobilizing novel chemical groups

Jennissen¹

1995

J of Molecular Recognition

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The cyanogen bromide and tresyl chloride (2,2,2-trifluoroethanesulfonyl chloride) methods belong to the best-known activation procedures for solid supports in biochemistry. In both cases the originally proposed reaction mechanisms were revised many years later. In this paper important aspects of these two major activation reactions in connection with the singular polysaccharide support, agarose, will be treated with emphasis on the novel reaction mechanism recently proposed for tresyl chloride. In addition, the special role played by sulfur in the new uncharged alkyl-S-S-gels is examined in connection with the phenomenon of base-atom recognition.

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Ortho and Para Substituted Derivatives of Benzotrifluoride

Cited by 85 publications

References 0 publications

Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives

Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives

Fluorine-Sacrificial Cyclizations as an Access to 5-Fluoropyrazoles

Cyanogen bromide and tresyl chloride chemistry revisited: The special reactivity of agarose as a chromatographic and biomaterial support for immobilizing novel chemical groups

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